Condensation products of hydrogenated naphthalenes with ethylene



PatentedJune 24, 1930 UNITED STATESPATENT OFFICE RICHARD MICHEL, OF KRIEIEELD, GERMANY, 'ASSIGNOR TO I, G. FARBENINDUSTBIE .AKTIENGESELLSCHAIT, OF FRANKFORT-ON-THE-MAIN, GERMANY, A. CORPORATION OF GERMANY CONDENSATION PRODUC'L S 0F HYDROGENA'IED NAIHTHALENES WITH ETHY'LENE No Drawing. Application filed April 7,1928, Serial 1705268563, and in Germany February 4, 1526.

The'present invention concerns the manufacture of condensation products from h-ydrogenated naphthalenes and derivatives thereof with ethylene and consists in cansing ethylene to interact with partially by dr ogenated naphthalenes or their deriva-' tives in the presence. of catalytically active substances at temperatures between 50 and 200 C. and under superatmospheric pressure. v p p According to the present invention ethylene can be readily introduced into the naphthalene nucleus by causing the reaction to 50 and 200 C. under superatmospheric pressure. As catalytic substances metallic vchlorides, by preference aluminium chloride and iron chloride are employed. They may advantageously be combined with other substances promoting the ease of reaction, such as benzene, hydrocarbons or halogen 'acids.

According to the operative conditions monoor poly-ethylated partially hydrogenated naphthalenes,, orby' more intensifiedaction, condensation products .in the form of highly viscous, strongly fluorescent oils, are. obtained. The process can also "be adapted to partially hydrogenated naphthalenes, which are. variously substituted.

The following example serves to illustrate the principles underlying my invention,

which as already stated can be carried out within wide limits a V Ewample: In an autoclave of 300 litres capacity 132 kgsof tetrahydronaphthalene and 2 kgs. of aluminium chloride are stirred forsome 4 hours with ethylene 'under a pressure of to atmospheres .andat about 100 Gav-The consumed ethylene is constantly replenished ,from a container under pressure until a total of 30 'kgs. has

been absorbed. After. cooling the contents of the autoclave and removin aluminium chloride, distillation is effected, preferably in 'vacun. The first fractions contain 10 .kgs. of unchanged tetrahydronaphthalene,-

' then 140 kgs. of oily product go over (b. p.

145 to 200 C. at 20 mm. pressure), while 5 kgs. of an undistillable residue remain.

The oily portion boils under,normal-pres- C. Instead of alumin-.

of my co-pending application Ser. No. '163,-

5T8, filed January 25, 1927. p

In the following claims the term partially hydrogenated naphthalene compound is intended to comprise the partial hydrogenation products of n'aphthalene,.or of its homologues' or substitution products. take place in the presence-0f catalytically acting substances at temperatures between 3. Process, which comprisesreacting with ethylene upon a partially hydrogenated naphthalene compound in the presence of a catalytically acting metallic chloride under superatmospheric pressure and at a temperature of about 100 C.

4. Process, which comprisesreactingwith ethylene upon tetrahydronaphthalene in the presence of a catalytically acting metallic 3 chloride underv a pressure of from 20 to 30 atmospheres 100 (3.

5. Process, which comprises reacting with and at a temperature of about ethylene upon tetrahydronaphthalene in the presence 0f aluminium chloride under a pressure of from 20 to 30 atmospheres and at a temperature of about 100 C.

' In' testimony whereof I have hereunto set my hand.

RlCHARD MICHEL. 

